A quantitative synthesis of β-carboxylated thiolophosphates via a Michael reaction

Reactions of O, O′-dialkylthiophosphoric acids with acrylates provide a direct synthetic route to β-carboxylated thiolophosphates. This Michael addition, without solvent, is quantitative at 90°C in 1 h for the 2/1 thiophosphoric acid/acrylate ratio. Moreover, this excess of thiophosphoric acid can b...

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Veröffentlicht in:Tetrahedron letters 2003-08, Vol.44 (33), p.6273-6276
Hauptverfasser: Desforges, Elisabeth, Grysan, Alexandre, Oget, Nicolas, Sindt, Michèle, Mieloszynski, Jean-Luc
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Sprache:eng
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Zusammenfassung:Reactions of O, O′-dialkylthiophosphoric acids with acrylates provide a direct synthetic route to β-carboxylated thiolophosphates. This Michael addition, without solvent, is quantitative at 90°C in 1 h for the 2/1 thiophosphoric acid/acrylate ratio. Moreover, this excess of thiophosphoric acid can be reused for further reactions. β-Carboxylated thiolophosphates are synthesized quantitatively via a Michael reaction between two equivalents of O, O′-dialkylthiophosphate acid and acrylate compounds.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)01530-2